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Waterbury Mayor Neil O'Leary Seeks 4th Term

The worst kept secret in Waterbury burst into the open this afternoon after Waterbury Mayor Neil O’Leary declared he will seek an historic 4th term in office this November.

“I've had a couple of job offers, some recently,” O’Leary told 300 business people and community leaders attending the annual “Mayoral Luncheon” event hosted by the Greater Waterbury Chamber of Commerce. “But I just have to tell you that I love it here. I love this job, and with your support I intend to run for mayor again in 2019.”

The news shocked no one in the room as O’Leary had hitched a cart before his horse by hosting a $1000 a plate fundraiser last night in downtown Waterbury.

No fortuneteller was needed. A $1000 a plate fundraiser at Drescher’s Restaurant had already announced to the world that O’Leary would seek another four years as mayor. The chamber announcement was a mere formality.

If he wins re-election and finishes the four-year term, O’Leary would have 12 years in office and become the longest continuously serving mayor in Waterbury history. Michael Jarjura and Edward “Mike” Bergin both served as mayor for ten straight years, so an O’Leary victory, if he finishes the term, would be historic.

Mayor O'Leary has made innovative decisions during his seven years in office, perhaps none so spontaneous as creating a "shovel brigade" of unemployed youth to help dig the city out from beneath a devastating Nor'easter. O'Leary wasn't sure if anyone would react to his call for action and was stunned when 700 people showed up at City Hall. The success of the shovel brigade drew national attention.

The renovation of Municipal Stadium is one of dozens of projects that have come to completion in the past seven years.

O'Leary was instrumental in having the City of Waterbury co-sponsor The Gathering, an annual festival that is now described as one the most culturally diverse festivals in New England.

O'Leary hired Vernon Riddick to become the first African American to lead the Waterbury Police Department. Riddick served for six years before leaving to become Police Chief in West Hartford. The current police chief is Fred Spagnolo, third from the left.

O'Leary has a terrific relationship with U.S. Senator Chris Murphy, left, and meets often with members of the state legislative delegation. Pictured here is former State Representative Victor Cuevas at a meeting.

O'Leary has a wonderful sense of humor and enjoys a hearty laugh many times a day.

Celebrating culture and dance at the annual Albanian Festival on Raymond Street in the South End.

When O’Leary ran in 2011 he vowed that if he were fortunate enough to win, and the electorate liked the job he was doing, he would serve six years in office (three two-year terms) and get out. But O’Leary had enough after four years and announced in July 2015 that he wasn’t seeking re-election. He was physically exhausted, and he was emotionally drained by the unexpected death of his close friend, Waterbury Police Captain Chris Corbett.

After four grinding years of chasing a hospital merger, securing millions of dollars in Brownfield funds, snagging a $14.4 million TIGER Grant, renovating the entire park system, expanding the grand list, changing the municipal healthcare plan, starting to build a new Public Works facility and helping to create the most culturally diverse festival in New England, Neil O’Leary was shot.

O'Leary is a very decisive man, which made his 2015 struggle to make a decision very difficult.

O’Leary’s announcement in 2015 that he was not seeking re-election stunned the political landscape. It was three weeks until the Democratic Party’s nominating convention and there was no replacement in sight. Private conversations with U.S. Senator Chris Murphy and Connecticut Governor Dan Malloy, the two most powerful Democrats in the state, convinced O’Leary to reverse his decision and climb back into the political ring.

O’Leary’s withdrawal at such a late date would have opened the door for former five-term Mayor Michael Jarjura – who had switched political parties in a showdown with O’Leary in 2011, and was now a Republican - to reclaim City Hall. Jarjura had universal name recognition in Waterbury, was independently wealthy, and also had the ability to raise money fast. Jarjura was also keen on developing projects in the East End of Waterbury, and not the Freight Street corridor or the Howland-Hughes project on Bank Street that Chris Murphy, Dan Malloy and Neil O’Leary backed. Neither Malloy nor Murphy had a good relationship with Jarjura, and with the possibility of their signature projects being derailed; they implored O’Leary to take one for the team.

And reluctantly, Neil O’Leary did.

In a three-way race that November O’Leary won 70% of the vote, and won the first four-year term in city history. There was widespread speculation in political circles that O’Leary would never finish the four-year term; he would become a state commissioner, he would enter into private business, or he would retire to Florida and fish with his buddies.

As Gomer Pyle used to say back in the 1960s TV sitcom, “surprise, surprise, surprise”; O’Leary is not only going to finish the four-year term, he’s going after another one.

Very few people I’ve spoken to in the past three years saw or felt this coming. The consensus was that Neil O’Leary was not going to seek re-election, and he would make that announcement at the last possible moment to shorten his lame duck period in office.

Having covered Waterbury City Hall for the past 25 years I can emphatically state that during that quarter century there was no mayor who worked harder that Neil O’Leary did during his first four years in office. He demanded a lot from his staff and department heads, and demanded even more from himself, all of which led him – and others - to the brink of burnout.

O’Leary’s past three years in office have not been as vigorous as he eased off the accelerator and tried to find a balance in managing major projects, finding time to watch his daughter’s sporting events, unwinding in Florida, and stretching his influence into regional and state circles. In addition to being the mayor of the 5th largest city in the state, O’Leary is the president of the Connecticut Conference of Municipalities (comprised of 168 elected officials from towns and cities in Connecticut), and is the chairman of the 19-town Naugatuck Valley Council of Governments. That is an extraordinary amount of influence locally, regionally and across the state of Connecticut.

O’Leary briefly flirted with the idea of running for Governor or Congress in 2018, but quickly concluded he had neither the passion or energy to mount a statewide or congressional district campaign.

Instead, Neil O’Leary loves Waterbury where he controls the political process as well as any mayor in recent memory. As the former police chief in Waterbury he has unusually strong connections to the leadership of the Waterbury Police Department, and O’Leary has insulated himself inside the Mayor’s Office by hiring old friends with life experience and loyalty to manage major projects, and keep the details out of his face.

Working for Neil O’Leary can be as thrilling as riding a Coney Island rollercoaster. He is demanding, he is funny and charming, he is intense. If he gets too intense some people decide to get off the rollercoaster, while others hang on and wait for a storm to pass. During today's Chamber luncheon O'Leary paused during his speech to publicly acknowledge his staff, which he admits he doesn't do nearly enough. "I was a cop for 30 years," O'Leary told the crowd, "and during that time I might have been told I was doing a good job three times. You just did your job."

When he's not smiling and laughing Neil O'Leary can be a stern taskmaster. No one working for the City of Waterbury wants to be on the receiving end of "the look."

O’Leary can get in your face and some political opponents have called him a bully and a dictator. He has bellowed at subordinates so loudly that visitors into Veterans Hall could hear his raised voice, and a few years ago the mayor almost came to blows with a local politician during a heated exchange inside his office.

Although O’Leary triggers a mix of fear and respect from municipal workers in Waterbury, down deep he relishes challenges and confrontations to his power, it gets his juices flowing. Days after the near-brawl inside his office O’Leary chuckled about the incident and said, “I love that stuff.”

In 2011 Neil O’Leary seized the Mayor’s Office away from five-term incumbent Mayor Michael Jarjura in one of the most contentious election battles in Waterbury history. The two political heavyweights threw left hooks and body blows at each other for months, and when the drama heightened 30 days before the election, they both crossed the line and hurled personal attacks at one another. It was an epic brawl.

O'Leary celebrating election night in 2011.

O'Leary forged close ties with Dan Malloy on the state level and Chris Murphy in Washington D.C. to capture funding needed to begin the long process of moving Waterbury forward.

O'Leary relies on State Senator Joan Hartley to lead the local delegation and to champion Waterbury in Hartford. They are pictured here at The Gathering as they entered Library Park in downtown Waterbury.

O'Leary roared his approval last August when Jahana Hayes won a bitter primary fight to secure the Democratic nomination for the 5th District in Congress. Three months later Hayes, a Waterbury native, made history as the first African-American to represent the Connecticut Democratic Party in Congress.

Which brings us to the 2019 mayoral race in Waterbury, which is forecast to be more of a victory lap than a brawl.

Republican alderman Vernon Matthews has already announced his intention to be on the mayoral ballot in November, either representing the GOP, or as an independent. Other Republicans might step into the fray, and certainly there will be a mayoral candidate from the Independent Party (perhaps Larry De Pillo will run a 7th time?)

Democrats with ambition will stand down and support O’Leary as they have little chance to match his fundraising prowess, his experience, or his mastery of the local political chessboard. Today Neil O’Leary made his official announcement before a cheering and supportive crowd at the Chamber luncheon and said all the right things about working hard and hoping the voters like the job he has done, and that he hopes they vote for him again in November.

The reality in Waterbury is that barring some unexpected twist, Neil O’Leary will cruise to re-election. The only real political drama in Waterbury will begin when O’Leary ends his historic reign as mayor - most likely on his own terms - and there is no telling when that will be.